I guess third time is the charm. Oryan finally responded with an actual answer to my question:
You can have up to 2 devices with one subscription. Keep in mind you will need to relicense tracks more often when you sync 2 devices.
To correct this problem, try relicensing the tracks within the Yahoo! Music Engine.
First, select your 'My Music' tab and locate the album with which you are experiencing this difficulty. Select the song and right click on it to bring up the song menu. Choose 'relicense track' to connect to our servers and refresh this songs license.
You may do this for multiple songs by shift-clicking each song in your list prior to right clicking the group.
Sounds it sounds possible to cut my subscription down from two accounts to one when our year is up, but it also sounds buggy. This also assumes the rules will not change.
Original post that started this